Water → (2-Aminopyridin-3-yl)methanol

HRID 2171959Notes

Reaction equation

HRID 2171959 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=1.O.[OH-].[Na+]>C1COCC1>[NH2:7][C:8]1[C:13]([CH2:14][OH:15])=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 729302-Aminonicotinic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 11159325(2-Aminopyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.4M lithium aluminum hydride in THF (181 mL g, 434 mmol) was added portionwise to a suspension of 2-amino-3-carboxypyridine (30.0 g, 217 mmol) in THF (350 mL) at 0° C. Once the addition was completed, the reaction mixture was stirred at room temperature for 15 minutes and then at reflux overnight. The mixture was then cooled to 0° C. and hydrolyzed by the successive addition of water (18 mL), a 1M solution of sodium hydroxide (18 mL) and water (50 mL). The resulting white suspension was stirred for one hour, filtered over Celite® and the cake was washed with THF (400 mL). After concentration to dryness of the filtrate, the title product was obtained as a light brown oil (25.1 g, 87%, py 93.1%).

Workup

  1. additionOnce the addition
  2. temperatureat reflux overnight
  3. stirringThe resulting white suspension was stirred for one hour
  4. filtrationfiltered over Celite®
  5. washthe cake was washed with THF (400 mL)
  6. concentrationAfter concentration to dryness of the filtrate

Sources & evidence

ORD record
ord-6ab9935aeadc4fc78bac3c63c8a7b7e2
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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